Chemistry of the natural order cupressales—41

Arya, V. P.; Erdtman, H.; Kubôta, Takashi

doi:10.1016/0040-4020(61)80076-8

Cited by 26 publications

(8 citation statements)

References 15 publications

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“…The geometry of the methyl ester group is normal. The result confirmed the strnctute proposed by Arya, Erdtman & Kubota (1961) and Thomas (1966). …”

supporting

confidence: 81%

“…trans-Communic acid has also been separated by chromatography from the bled resin of New Zealand kauri (Thomas, 1966). (Arya, Erdtman & Kubota, 1961;Thomas, 1966) that trans-communic acid is difficult to purify and polymerizes very easily, and that it had not been obtained in a crystalline form. Thus, it was converted into its methyl ester.…”

mentioning

confidence: 99%

“…1 (Arya, Erdtman & Kubota, 1961). trans-Communic acid has also been separated by chromatography from the bled resin of New Zealand kauri (Thomas, 1966).…”

mentioning

confidence: 99%

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Structure of methyl trans-communate

Lee¹,

Lin²,

Cheng³

et al. 1987

Acta Crystallogr C

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Discussion. Since the NMR spectrum of the isolated compound [taiwanxan, (II), m.p. = 500-503 K] indicates three acetyl groups (2.016, 2.028, 2.039) and an ct-methylbutyrate group (0.88, t, J = 7.4 Hz; 1.11, d, J = 7 HZ), the structure is very similar to the known compound (I) (De Marcano & Halsall, 1969), taxa-4(20),11-diene-2a,5 et,7fl,9o., 10fl-pentol 7fl,9a,10fl-triacetate 2~t-ct-methylbutyrate, C31H4609, m.p. = 500-502 K. The structure of taiwanxan, (II), was revealed by X-ray single-crystal diffraction studies as taxa-4(20), 11-diene-2a,5a,9a,10ft, 14fl-pentol 2a,9a, 10fl-triacetate 14fl-a-methylbutyrate.

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“…The geometry of the methyl ester group is normal. The result confirmed the strnctute proposed by Arya, Erdtman & Kubota (1961) and Thomas (1966). …”

supporting

confidence: 81%

mentioning

confidence: 99%

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Structure of methyl trans-communate

Lee¹,

Lin²,

Cheng³

et al. 1987

Acta Crystallogr C

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“…According to the authors it belongs to the ent-labdane series and therefore is a stereoisomer of 1. To establish the absolute configuration of 1, its experimental ECD spectrum ( Figure 3) was recorded and compared with those registered for compounds 3 and 4 ( Figure 3), whose stereochemistry has been previously determined [16]. The ECD spectrum of 1 displayed a negative Cotton effect at 203 nm and a positive one at 226 nm and was in good agreement with those of 3 and 4.…”

Section: Resultsmentioning

confidence: 56%

“…The 13 C NMR spectrum (Table 1) of 1, corroborated the presence of 23 carbon atoms, which, according to the HSQC spectrum correspond to ten methylenes (two sp 2 and eight sp 3 ), four methines (two sp 2 and two sp 3 ), two quaternary carbons, four nonprotonated carbons and three methyl groups. In the 13 C NMR spectrum of 1 (Table 1), signals for an exocyclic methylene, such as the one present at C-8:C-17 of trans-communic acid (3) [16] and trans-communol (4) [16] are observed at δ 147.7 (C) and 108.2 (CH 2 ) ppm. Observed signals for carbon atoms of a terminal vinyl group at δ 141.7 (CH) and 110.1 (CH 2 ), together with those observed at 133.8 (CH), 133.7 (C), 23.3 (CH 2 ) and 12.0 (CH 3 ), suggested that compound 1 has a side chain identical to the one present in diterpenes 3 and 4.…”

Section: Resultsmentioning

confidence: 99%

Structural Elucidation of Malonylcommunol and 6β-Hydroxy-trans-communic Acid, Two Undescribed Diterpenes from Salvia cinnabarina. First Examples of Labdane Diterpenoids from a Mexican Salvia Species

et al. 2020

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The aerial parts of Salvia cinnabarina afforded two undescribed labdane diterpenoids 1 and 2 (malonylcommunol and 6β-hydroxy-trans-communic acid) along with two known labdane diterpenoids, trans-communic acid (3) and trans-communol (4). Additionally, seven known metabolites were also isolated; two isopimarane diterpenoids 5 and 6, two sesquiterpenoids identified as β-eudesmol (7) and cryptomeridiol (8), and three aromatic compounds identified as phthalic acid (9), a mixture of tyrosol fatty acid esters (10) and the flavone salvigenine (11). While compounds compounds 1-3 showed significant inhibition of yeast α-glucosidase, compounds 2, 3 and 7 had no anti-inflammatory activity in the edema model induced by TPA. This paper is not only the first report on a wild population of Salvia cinnabarina, but also of the presence of labdane-type diterpenoids in a Mexican Salvia sp.Molecules 2020, 25, 1808 2 of 17 spectroscopic and X-ray diffraction analysis [7,8]. Compound 12 has been tested in several in vitro and in vivo models and exhibits a wide array of biological activities, such as antispasmodic in the isolated guinea-pig ileum model, inhibition of urinary bladder contractility in rats [9] and intestinal motility in mice [10]. Hypotensive activity in a rat model [11], along with anxiolytic and anti-depressive effects in the elevated plus-maze and the forced swimming tests in mice have also been described [12]. Compound 12 showed antimutagenic activity in the Ames test on Salmonella typhimurium and Escherichia coli [13] and also had an anticlastogenic effect in human lymphocytes of its sodium salt [14]. It should be noted that, up to now, all the studies on S. cinnabarina, have been carried out solely on cultivated material from different Botanical Gardens.Continuing with our systematic study of the genus Salvia in Mexico, and ongoing investigation for biological activity diterpenes of chemosystematic importance [15], we report herein the first study on a wild population of S. cinnabarina collected in the State of Puebla (Mexico). Several diterpenoids of the labdane (1-4) and isopimarane (5-6) skeletons were isolated, as well as two eudesmane-type sesquiterpenoids (7-8), phtalic acid (9), tyrosol derivatives (10) and the flavone salvigenin (11). Compounds 1-2 proved to be undescribed labdane-type diterpenoids related to trans-communic acid (3) and trans-communol (4), also isolated from this plant, and their structures were established as malonylcommunol (1) and 6β-hydroxy-trans-communic acid (2). While compounds 1-3 showed significant inhibition of yeast α-glucosidase, compounds 2,3 and 7 showed no anti-inflammatory activity in the edema model induced by TPA. Results and DiscussionThe aerial parts of Salvia cinnabarina afforded 11 compounds (Figure 1) after extensive chromatographic separation and purification.Molecules 2020, 25, x FOR PEER REVIEW 2 of 17

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